3-(2,6-Dichlorophenyl)-4-formyl-5-isoxazolecarbonyl chloride → 3-(2,6-Dichlorophenyl)-N-(5-{4-[3-(isobutyrylamino)phenyl]-1-piperidinyl}pentyl)-5-methyl-4-isoxazolecarboxamide

Participants

Reaction Steps

A mixture of 3-(2,6-dichlorophenyl)-4-formyl-5-isoxazolecarbonyl chloride (69.0 mg, 0.250 mmol), N-{3-[1-(5-aminopentyl)-4-piperidinyl]phenyl}-2-ethylpropanamide (44.0 mg, 0.150 mmol), TEA (30.0 mg, 0.300 mmol) in THF (2 mL) was stirred for 12 h at room temperature. The crude product was purified by preparative TLC using CH2Cl2/MeOH/isopropyl amine (19:1:0.2) to give the desired product (52 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 7.52–7.49 (m, 2H), 7.49–7.41 (m, 2H), 7.39–7.31 (m, 2H), 7.29–7.21 (m, 2H), 6.92 (d, 1H, J=7.6 Hz), 3.25–3.11 (m, 5H), 2.81–2.74 (m, 4H), 2.58–2.44 (m, 4H), 2.30–2.19 (m, 2H), 1.93–1.78 (m, 4H), 1.56–1.44 (m, 2H), 1.31–1.28 (m, 2H), 1.24 (d, 6H, J=6.6 Hz); ESMS m/e: 585.2 (M+H)+.

Provenance & Evidence